Cas no 26001-38-7 (8-Thioguanosine)

8-Thioguanosine is a modified nucleoside analog in which the oxygen atom at the 8-position of guanosine is replaced by sulfur. This structural alteration enhances its reactivity and binding properties, making it valuable in biochemical and pharmaceutical research. The compound exhibits unique electronic and steric characteristics due to the thione group, which can influence base-pairing interactions and stability in nucleic acid systems. It is particularly useful in studies involving RNA modification, enzyme inhibition, and nucleoside-based drug development. Its ability to act as a precursor for thiolated nucleotides further expands its utility in probing nucleic acid structure and function. 8-Thioguanosine is also explored for its potential therapeutic applications, including antiviral and anticancer research.
8-Thioguanosine structure
8-Thioguanosine structure
Product Name:8-Thioguanosine
CAS No:26001-38-7
MF:C10H13N5O5S
MW:315.305720090866
CID:264561
PubChem ID:135457302
Update Time:2025-06-11

8-Thioguanosine Chemical and Physical Properties

Names and Identifiers

    • Guanosine,7,8-dihydro-8-thioxo-
    • 2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanylidene-3,7-dihydropurin-6-one
    • 8-Mercaptoguanosine
    • 8-THIOGUANOSINE
    • 8-mercapto-guanosine
    • NSC 79216
    • SQ 12760
    • 7,8-Dihydro-8-thioxoguanosine
    • 8-SH-Guo
    • B0T9FOW56N
    • 2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-mercapto-1H-purin-6(9H)-one
    • C10H13N5O5S
    • 8-Mercapto-D-guanosine
    • Q27274231
    • 2-Amin
    • 2-AMINO-9-[3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-8-SULFANYLIDENE-6,7,8,9-TETRAHYDRO-1H-PURIN-6-ONE
    • EINECS 247-402-4
    • 2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-thioxo-1,7,8,9-tetrahydro-6H-purin-6-one
    • Guanosine, 7,8-dihydro-8-thioxo-
    • MFCD00057038
    • UNII-B0T9FOW56N
    • SCHEMBL54408
    • 26001-38-7
    • SR-01000147753
    • SR-01000147753-1
    • NSC817320
    • 2-amino-9-[(2R, 3R, 4S, 5R)-3, 4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanylidene-1, 7-dihydropurin-6-one
    • CHEMBL2311184
    • 2-AMINO-9-[(2R,3R,4S,5R)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-8-SULFANYLIDENE-1,7-DIHYDROPURIN-6-ONE
    • 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-thioxo-8,9-dihydro-1H-purin-6(7H)-one
    • AC-32333
    • DTXSID00365121
    • AS-61194
    • AKOS001714888
    • 29836-03-1
    • NSC-79216
    • GUANOSINE, 8-MERCAPTO-
    • KZELNMSPWPFAEB-UMMCILCDSA-N
    • 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanylidene-6,7,8,9-tetrahydro-1H-purin-6-one
    • NSC-817320
    • NS00050968
    • MFCD01081756
    • AKOS030489379
    • G75966
    • DB-229709
    • DTXCID50316163
    • 8-Thioguanosine
    • Inchi: 1S/C10H13N5O5S/c11-9-13-6-3(7(19)14-9)12-10(21)15(6)8-5(18)4(17)2(1-16)20-8/h2,4-5,8,16-18H,1H2,(H,12,21)(H3,11,13,14,19)/t2-,4-,5-,8-/m1/s1
    • InChI Key: KZELNMSPWPFAEB-UMMCILCDSA-N
    • SMILES: S=C1NC2C(NC(N)=NC=2N1[C@H]1[C@@H]([C@@H]([C@@H](CO)O1)O)O)=O

Computed Properties

  • Exact Mass: 315.06400
  • Monoisotopic Mass: 315.064
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 6
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 2
  • Complexity: 578
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 185
  • XLogP3: -3

Experimental Properties

  • Density: 2.35±0.1 g/cm3 (20 oC 760 Torr),
  • Melting Point: >220 oC
  • Boiling Point: 595.1°Cat760mmHg
  • Flash Point: 313.7°C
  • Refractive Index: 2.024
  • Solubility: Almost insoluble (0.019 g/l) (25 o C),
  • PSA: 199.30000
  • LogP: -2.05560

8-Thioguanosine Security Information

  • WGK Germany:3
  • Storage Condition:2-8°C

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8-Thioguanosine Suppliers

Amadis Chemical Company Limited
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Purity:99%
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Price ($):366.0/549.0/914.0
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Additional information on 8-Thioguanosine

8-Thioguanosine (CAS No. 26001-38-7): A Versatile Compound in Chemical and Biological Research

8-Thioguanosine (CAS No. 26001-38-7) is a modified nucleoside that has garnered significant attention in the fields of chemical and biological research due to its unique properties and potential applications. This compound is a sulfur-substituted analog of guanosine, where the oxygen atom at the 8-position of the guanine base is replaced by a sulfur atom. This subtle modification can have profound effects on the biological activity and stability of nucleic acids, making 8-Thioguanosine an intriguing subject for various scientific investigations.

The structural modification in 8-Thioguanosine has been shown to enhance its resistance to enzymatic degradation, which is a critical factor in the development of therapeutic agents and diagnostic tools. Recent studies have demonstrated that this compound can be used to stabilize RNA molecules, thereby extending their half-life and improving their efficacy in various applications. For instance, a study published in the Nucleic Acids Research journal highlighted the use of 8-Thioguanosine-containing oligonucleotides in RNA interference (RNAi) technology, where it significantly improved the stability and potency of siRNAs.

In addition to its role in RNA stabilization, 8-Thioguanosine has also been explored for its potential as an antiviral agent. Research conducted by a team at the University of California, San Francisco, revealed that 8-Thioguanosine can inhibit the replication of certain viruses by interfering with their RNA-dependent RNA polymerases. This finding opens up new avenues for the development of antiviral therapies targeting RNA viruses, such as influenza and hepatitis C.

The pharmacological properties of 8-Thioguanosine have also been investigated in the context of cancer research. Studies have shown that this compound can induce apoptosis in cancer cells by disrupting key signaling pathways involved in cell survival and proliferation. A notable study published in the Cancer Research journal demonstrated that 8-Thioguanosine-based prodrugs could selectively target and kill cancer cells while sparing normal cells, suggesting its potential as a novel anticancer agent.

Beyond its therapeutic applications, 8-Thioguanosine has found utility in synthetic biology and biotechnology. The ability to incorporate this modified nucleoside into synthetic DNA and RNA molecules allows researchers to create custom-designed nucleic acids with enhanced stability and functionality. This has significant implications for the development of advanced diagnostic tools, such as biosensors and molecular beacons, which require high stability and specificity.

The synthesis of 8-Thioguanosine involves several well-established chemical reactions, including nucleophilic substitution and coupling reactions. Recent advancements in synthetic chemistry have led to more efficient and scalable methods for producing this compound, making it more accessible for both academic research and industrial applications. For example, a study published in the Tetrahedron Letters journal described a novel one-pot synthesis method that significantly reduced the number of steps required to produce high-purity 8-Thioguanosine.

The safety profile of 8-Thioguanosine is another important consideration for its widespread use. Extensive toxicological studies have shown that this compound exhibits low toxicity at therapeutic concentrations, making it suitable for use in both preclinical and clinical settings. However, as with any new chemical entity, ongoing safety evaluations are essential to ensure its long-term safety and efficacy.

In conclusion, 8-Thioguanosine (CAS No. 26001-38-7) is a versatile compound with a wide range of applications in chemical and biological research. Its unique structural properties make it an attractive candidate for developing novel therapeutic agents, diagnostic tools, and biotechnological applications. As research continues to uncover new insights into its mechanisms of action and potential uses, the future prospects for this modified nucleoside appear promising.

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Amadis Chemical Company Limited
(CAS:26001-38-7)8-Thioguanosine
A855706
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Price ($):366.0/549.0/914.0
Email
NewCan Biotech Limited
(CAS:26001-38-7)8-Thioguanosine
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Quantity:10g
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